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902489

Sigma-Aldrich

Tris(trimethylsilyl)silanol

≥95%

Synonym(s):

(Hydroxy-bis(trimethylsilyl)silyl)-trimethylsilane, (TMS)3SiOH, 1,1,1,3,3,3-Hexamethyl-2-(trimethylsilyl)trisilan-2-ol, Supersilanol

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About This Item

Empirical Formula (Hill Notation):
C9H28OSi4
CAS Number:
7428-60-6
Molecular Weight:
264.66
MDL number:
MFCD00093727
UNSPSC Code:
12161700
NACRES:
NA.22
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Assay

≥95%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n/D 1.496

density

0.859 g/mL

SMILES string

[Si]([Si](C)(C)C)([Si](C)(C)C)([Si](C)(C)C)O

InChI

1S/C9H28OSi4/c1-11(2,3)14(10,12(4,5)6)13(7,8)9/h10H,1-9H3

InChI key

ABTWCNHNRLMBFR-UHFFFAOYSA-N

Application

Under a dual catalytic copper/photoredox manifold, this supersilanol has been demonstrated by the MacMillan lab to be an excellent reagent for the trifluoromethylation of alkyl halides and aryl halides to yield alkyl-CF3 and aryl-CF3 in high yields. In both cases, these reactions exhibit wide substrate scope with good functional group tolerance. More specifically, a variety of 5-membered and 6-membered heteroaryl halides can be readily converted to the corresponding trifluoromethylheteroarenes under mild conditions. To be use in conjunction with dMesSCF3 (901466) and Ir photocatalyst (902217 or 902225).

Other Notes

A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

200.3 °F

Flash Point(C)

93.5 °C

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0225
MKCW6219
MKCS7963
MKCQ7737
MKCN9702

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Annie J Jiang et al.
Journal of the American Chemical Society, 131(46), 16630-16631 (2009-11-19)
Mo and W MonoAryloxide-Pyrrolide (MAP) olefin metathesis catalysts can couple terminal olefins to give as high as >98% Z-products in moderate to high yields with as little as 0.2% catalyst. Results are reported for 1-hexene, 1-octene, allylbenzene, allyltrimethylsilane, methyl-10-undecenoate, methyl-9-decenoate
Timothy J Boyle et al.
Inorganic chemistry, 57(15), 8806-8820 (2018-07-07)
In an effort to generate single-source precursors for the production of metal-siloxide (MSiO x) materials, the tris(trimethylsilyl)silanol (H-SST or H-OSi(SiMe3)3 (1) ligand was reacted with a series of group 4 and 5 metal alkoxides. The group 4 products were crystallographically
Chip Le et al.
Science (New York, N.Y.), 360(6392), 1010-1014 (2018-06-02)
Transition metal-catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a

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